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A regiospecific radical annulation strategy to functionalised chiral bicyclo[3.3.l]nonanes

Srikrishna, A and Hemamalini , P and Venkateswarlu, S (1994) A regiospecific radical annulation strategy to functionalised chiral bicyclo[3.3.l]nonanes. In: Tetrahedron, 50 (29). pp. 8781-8792.

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Official URL: http://dx.doi.org/10.1016/S0040-4020(01)85352-7


A radical annulation, i.e. an intermolecular radical Michael addition followed by an intramolecular Michael addition of the resultant radical (radical cyclisation) has been employed for the construction of chiral functionalised bicyclo[3.3,1]-nonanes. Thus reaction of carvone hydrohalides 7 with (n)Bu(3)SnH and AIBN in the presence of excess of radicophiles 4 furnished, regiospecifically bicyclo[3.3.1]nonanes 8-14, introducing three new chiral centres in a stereoselective manner. Analogously the bromide 18 generated the bridgehead substituted bicyclo[3.3.1]-nonanes 19-21.

Item Type: Journal Article
Publication: Tetrahedron
Publisher: Elsevier Science
Additional Information: Copyright of this article belongs to Elsevier science.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 25 Mar 2011 06:37
Last Modified: 25 Mar 2011 06:37
URI: http://eprints.iisc.ac.in/id/eprint/36288

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